Electrochemical enantioselective sensor for effective recognition of tryptophan isomers based on chiral polyaniline twisted nanoribbon

Highlights: • Polyaniline with chiral nanospace has been successfully fabricated through chemical oxidation. • Chiral polyaniline modified electrode was used for chiral discrimination of tryptophan isomers. • Chiral polyaniline modified electrode showed excellent enantioselectivity towards chiral amino acids. Effective enantioselective recognition with chiral nanomaterials remains a challenge in the field of chemistry and biology. In this paper, a pair of left- and right-handed polyaniline (defined as S-PANI and R-PANI) were synthesized by chemical oxidation of aniline to form a specially twisted nanoribbon, which was induced by enantiomeric camphorsulfonic acid. Both S-PANI and R-PANI were used to construct electrochemical chiral sensors for the discrimination of tryptophan isomers (D- and L-Trp). Owing to the formation of efficient chiral nanospace with special nanoribbon morphology and enormous amounts of oxygen-containing functional groups of S-PANI or R-PANI, the high enantioselectivity was obtained with the recognition efficiency of 4.90 (D-Trp) on S-PANI and 4.20 (L-Trp) on R-PANI, respectively. The obtained chiral electrodes were also used for the determination of the enantiomeric excess (ee) for Trp, and a good linear relationship between peak currents and ee% of Trp was obtained. Furthermore, the strategy we proposed has tremendous potential in enantiomer recognition field.